Unprotected Xylose‐Derived Nitrone in Stereodivergent Synthesis of 4‐Hydroxypiperidine Enantiomers: Weak Lewis Acid Induced Alteration of Stereochemistry in 1,3‐Dipolar Cycloaddition | Zendy

Rowicki Tomasz | Zendy; Malinowski Maciej | Zendy; Gryszel Maciej | Zendy; Czerwińska Karolina | Zendy; Madura Izabela | Zendy; MironiukPuchalska Ewa | Zendy; KoszytkowskaStawińska Mariola | Zendy; Sas Wojciech | Zendy

Premium

Unprotected Xylose‐Derived Nitrone in Stereodivergent Synthesis of 4‐Hydroxypiperidine Enantiomers: Weak Lewis Acid Induced Alteration of Stereochemistry in 1,3‐Dipolar Cycloaddition

Author(s) -

Rowicki Tomasz,

Malinowski Maciej,

Gryszel Maciej,

Czerwińska Karolina,

Madura Izabela,

MironiukPuchalska Ewa,

KoszytkowskaStawińska Mariola,

Sas Wojciech

Publication year - 2015

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201403410

Subject(s) - chemistry , nitrone , cycloaddition , lewis acids and bases , enantiomer , bicyclic molecule , chiral lewis acid , piperidine , stereochemistry , 1,3 dipolar cycloaddition , intramolecular force , enantioselective synthesis , enantiomeric excess , organic chemistry , catalysis

A one‐pot, two‐step synthesis of chiral 7‐oxa‐1‐azabicyclo[2.2.1]heptane derivatives from unprotected D ‐xylose was achieved by an intramolecular 1,3‐dipolar cycloaddition of the N ‐(γ‐alkenyl)‐substituted nitrone intermediate. The stereochemical course of the cycloaddition was altered by the addition of an achiral Lewis acid. The bicyclic byproducts were employed in a concise synthesis of two new enantiomeric piperidine‐type iminosugars.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research